How to Pick a Career (That Actually Fits You) - Wait But Why

If you can figure out how to get a reasonably accurate picture of the real career landscape out there, you have a massive edge over everyone else, most of whom will be using outdated conventional wisdom as their instruction booklet.

Careers used to be kind of like a 40-year tunnel. You picked your tunnel, and once you were in, that was that. You worked in that profession for 40 years or so before the tunnel spit you out on the other side into your retirement.

Today’s career landscape isn’t a lineup of tunnels, it’s a massive, impossibly complex, rapidly changing science laboratory.

• Time. A typical career will take up somewhere between 20% and 60% of your meaningful adult time.
• Quality of Life. Your career has a major effect on all your non-career hours.
• Impact. Whatever shape your career path ends up taking, the world will be altered by it.
• Identity. We tell people about our careers by telling them what we are.

1. List careers you want/find desirable.
2. List all careers that are realistic to potentially achieve.
3. Find the overlapping areas between what is desirable, and what is possible.

1. Personal. The human need for fulfilment.
2. Social. Diverse social desires that want to be relevant, important, widely known, accepted, well-liked and agreeable.
3. Lifestyle. The desire to have a stress-free life.
4. Moral. The desire to do something philanthropic, or to display altruistic behaviour.
5. Practical. The desire to look after your practical needs, like food, clothing, housing.

• Play the Why Game: Why is this something I want? 
• Look at your Denial Prison: Uncovering your authentic wants that are repressed.
• Priority Rankings: Almost as important as the wants themselves is the priority they’re given.

• Broad landscape. The landscape today is made up of thousands of options and the way things work today, if there’s an option you want that’s not already out there, you can probably create it for yourself.
• Specific Career Path. A career path is like a game board. The conventional wisdom bookshelf contains instruction booklets for only a small fraction of today’s available game boards—and those that it does have usually tell you how that game was played in the past, even though the current game board has evolved significantly into something with new kinds of opportunities and different rules and loopholes.

When assessing your chances on a certain career path, the key question is: With enough time, could you get good enough at this game to potentially reach whatever your definition of success is in that career?

After considering

• The general landscape
• Specific careers
• Where your Starting point is (based on your current skills, resources, and connections relevant to that field)
• Your Success point/End point
• Your estimate of your pace of improvement
• Your level of persistence

you are able to plot your career path forward.